In his Editor’s Letter, Vanity Fair editor Graydon Carter remarks on the magazine’s milestone: “In an age when nothing seems to last—not convictions, not even cities—a centennial, like the one Vanity Fair celebrates this year, makes me marvel at the simple fact of longevity.”

“Magazines have ‘bones’—the unchanging elements that give structure to creativity—as surely as gardens and houses do,” writes Carter. “Today’s magazine is different in countless ways from yesterday’s—as even the briefest excursion through this issue will show. But I like to think that if [Vanity Fair’s first editor] Frank Crowninshield…could see the modern Vanity Fair, stripped of its logo and other identifying marks, he’d know in an instant what he held in his hands.”

Inside the issue, Leibovitz photographs Upton lounging on the moon, mimicking the illustration on the original cover of Dress & Vanity Fairfrom October 1, 1913. Upton tells contributing editor Jim Windolf that her road to success wasn’t always easy: “I’m not going to name names, but one agency told me, ‘You’re too American, and everybody knows American women are lazy.’ I was so offended! I’ve never been so offended! I was like, ‘You know that you’re in America, right?’ And it wasn’t ‘American models’—it was ‘American women are lazy,’ period! I feel like a lot of women would disagree with that. A lot!”

Elsewhere in the issue, the editors collected many of the magazine’s most iconic images—including portraits by Leibovitz, Mario Testino, Bruce Weber, and Edward Steichen, plus illustrations from the Jazz Age. To mark the century, Carter also commissioned 10 essayists to write about each decade of the magazine’s life. They include: Bill Maher, Dave Eggers, Kurt Andersen, Lorne Michaels, Robert Stone, Jan Morris, Daniel Okrent, Laura Hillenbrand, A. Scott Berg, and Julian Fellowes.